Vat dyestuffs of the anthraquinoneacridone series



Patented Nov. 21, 1939 VAT DYESTUFFS OF THE AN THRAQUINONE- ACRIDONE SERIES Erwin Kramer, Oologne-Deutz, Germany, assign- W or to-General Aniline Works, Inc-, ew York,

N. Y., a corporation of Delaware No Drawing. Application January 4, 1939, Serial. No. 249,253. In Germany January 7, 1938 4' Claims. (01. 260-277) The present invention relates to new vat dyestuffs of the anthraquinone acridone series.

I have found that new and valuable vat dyestufis are obtained by causing a -halogen-anthraquinone-acridone to react with a 2-(4'--aminophenyl) -anthraquinone. The reaction is preferably carried out in the presencegof an organic solvent as, for instance, nitrobenzene or naphthalene, atv an elevated temperature and in the presdistinguished by excellent iastness properties especially to chlorine.

The following examples illustrate the invention without, however, restricting it thereto, the parts being by weight:

Example 1 18 parts" of 4 chloro-janthraquinone 2,1 7 (N) 1 ,2'-(N) -benz'eneacridone, f j 45 parts of 2- (4' aminophehyl) -anthraquinone,

7 parts of potassium carbonate and 0.5 part of cuprous chloride I are heated to boiling in 50 parts of naphthalene for 8 hours. The reaction mixture is diluted with 10 ence of an acid-bindingagent, such as an alkali Py filtered w t t o at a temperaiture salt of a weak acid, as, for instance, sodium carf and Washed Wlth Pyrmme Water n d i bonate, potassium carbonate or sodium acetate. hydrochlorlc acid The dyestufi is Obtainedm The addition of copper powder or a copper salt form of needles, Which sotluble in as, for example, cuprous chloride or copper ace-' Sulfuric acld .Wlth a browhreh if It tate,'as a catalyst hasproved to be advantageous. dyes cotton m a red-brown Vat ohve Shades As valuable starting materials of the character of Y good t Washing, boiling and to 15 stated above there may be mentioned 4-chloror anthraquinone-2,1(N)-1,2'- (N) -benzeneacriv E- p 2 done, -t c q ll 22 parts or 4,3',5-trichloro-anthraquinone-2,1- Y

(N) -benzel}eacrldone and (N)-1',2-(N) -benzeneacridone,

0h10r0- anth1aqumne-2,1-(N) 3 (N) 30 parts of 2-(4='-aminopheny1)-anthroquinone, Zeneacrldone- 16 parts of anhydrous sodium acetate and My new dyestuffs correspond to the following 0 part of copper acetate general formula" are heated to boiling in 200 parts of naphthalene 25 X for 7 hours. After diluting the melt with pyridine it is filtered with suction at 90 and the resi- X X due is washed with hot pyridine until the running ofi is colorless. Then the dyestufi is extracted with hot water and hot dilute hydrochloric acid a p and for further purification it is boiled out with 30 H L 150 parts of nitrobenzene after drying. The dye- I stufi thus obtained represents small olive needles soluble in sulfuric acid with a brown-orange col- I oration. It yields on cotton from a brown vat O olive-green shades of excellent fastness properll ties to washing, boiling and to chlorine.

EN Example 3 12 parts of 4,3',4',5'-tetrachloro-anthraquinone- 40 o 2,1-(N) -1,2'-(N) -benzeneacridone, 40

15 parts of 2-(4-aminophenyl)-anthraquinone,

3 parts of potassium carbonate, 0.1 part of copper and wherein X stands for halogen or hydrogen. They dye vegetable fibers olive-green shades which are part of copper acetate are heated to boiling in 100 parts of naphthalene for 7 hours. After diluting the reaction mixture with dichlorobenzene orpyridine, the dyestufi is filtered with suction at 90 and washed with pyridine until the running ofi is colorless. Then the 3 whereinX standsfor a member of the group consisti'ng of hydrogen andhal'oge'n.

2. The compound of the following formula 3. The compound of the following formula 4. The compound of the following formula OHI(\1 II 0 II I OHN- 

